As a Personal Stylist and Personal Shopper many people tell me that deciding what to put on their feet can be the most challenging part of pulling together an outfit. Deciphering which style of boot will suit your body shape and fashion personality as well as work with whatever item of clothing you happen to be wearing may appear tricky. But follow a few simple rules and all will become clear.

Here to help take away any uncertainty, is a list of all the key style elements you need to consider when choosing the right pair of winter boots for you.

Ankle Length (Shoe boots)

Good for…

Women with a very shapely leg – as the fit should not be a problem. Opt for one with a heel and team with some vertically detailed tights and you’ll instantly create a leaner shaped leg.

Ankle Boot with Heel & Striped Tights

Women with proportionally short legs – I recommend you only wear this style with dresses or keep regular cut trousers tucked out over the boot.

Women conscious of comparatively skinny or shapeless ankles – then the ankle boot provides a useful cover that masks this aspect.

Men conscious of having slim legs – you will favour a more streamlined boot, whereas men with larger more muscular legs will really suit clumpier boots style (e.g. a brogue boot or workman boot)

How to wear them…

Offering a stylish alternative to shoes, these have become a staple for both men and women all year round.

Men Those men wanting to finish off their sleek, urban look will do well to choose the streamlined Chelsea boot, once a mod staple, Wiggo will no doubt be sporting a pair this winter.

Streamlined Chelsea Boot

For an edgy, more casual look try a vintage/distressed effect boot – allowing you to smarten up jeans whilst not having to wear a more formal shoe.

If you’ve been drawn to the preppy look and have enjoyed wearing your colourful chinos turned up with boat shoes, you can maintain this look whilst keeping your ankles warm with the boat boot. Or if you fancy something different, try the desert boot style.

Boat Boot (From Office)Distressed Desert Boot

Men who seek more of a statement boot can opt for elaborate embellishments, alternative patterned fabrics or perhaps a heel.

Statement Boot (Gucinari)

Women Ankle / shoe boots offer a grown-up, edgy look which can knock out the prettiness of dresses and skirts, this style is often favoured by those drawn to a slightly tomboyish/androgynous look.

Edgy Ankle Boot Look

That said, a spiked heel will give this boot a sexy feminine edge. Whereas a pretty colour, a feminine ruffle or vintage-esque lace-up detail can instantly inject some girlishness into the boot.

Spiked Heel Lace-up BootPretty Colour with Feminine Ruffle

Calf length

Good for…

Men & Women with a particularly slender calf – will find this length can enhance their calf shape, although be careful not to choose a style which is particularly wide (or clump) for if they look like they’re swimming in the boot it’ll only serve to accentuate the narrowness of your calf.

Women with proportionately long legs – worn over trousers or with skirts this length is also the most effective way of shortening the leg.

Shortening Calf Length Boot

Not good for…

Women with shapely calves – if ,like me, you have a rather shapely/muscular (ahem) calf this length will do you no favours – keep the length above or below the calf.

How to wear them…

The grungy biker or military boot is probably the most popular calf length style on the high street for men and women.

Men

These statement casual boots work best worn slightly open over puckered up jeans. Team with a chunky knit jumper and leather jacket for a stylishly edgy look.

Casual Calf Length Boot

Women

This style can toughen up a more playful look, when worn with feminine dresses – more cute than pretty.

Tough yet Cute Calf Length Boots

Equally, it can add real edge to pair of straight leg or skinny jeans, offering an alternative to the classic knee length riding boot.

Edgy Calf Length Boots with Jeans

Knee length

Good for…

Most women – Still the length of choice for many women on cold winter days, this is generally a flattering length for all women depending on how you wear them.

Women with very long legs – You can shorten the leg by wearing them over leggings, jeans or trousers.

Not good for…

Men with proportionately shorter legs

How to wear them…

Men

Generally this length of boot will be more a practical choice for men on particularly wet days or when out in the countryside.

Knee Length Boots

Of course those who seek to make more of a statement, may very well be drawn to this more unconventional length of boot for men:

Statement Knee Length Boots

Women

The classic riding boot offers a very wearable way to dress down a dress or skirt – allowing you to really maximise these items.

Classic Riding Boot

Another, more traditional way, is over skinny jeans for a very practical and relaxed look.

Knee Length Boot with Skinny Jeans

This style I would recommend more for casual daytime looks and particularly wet weather. Of course when it’s really wet, the ultimate knee high boot is the welly (my aubergine Hunter wellies got more outings than usual this year, despite there being no Glastonbury).

Knee Length Casual Boot

However, if you seek a dressier look, opt for knee length boots with a heel.

Knee Length Boot with Heel

Over-the-knee length

Good for…

Generally a style best left for women – who have proportionally long and/or relatively slender legs.

How to wear them…

Men

This length is more for the preserve of women, and as such you’ll do well to even find a pair on the high street. Generally this style is more for your metro-sexual man, looking to make a statement.

Over The Knee Boot

Women

Transform a simple skinny jean outfit into a sexy casual look, with a high-heeled pair.

High Heeled Over The Knee Boot

For an equally sexy look, wear your over-the-knee heeled boots with a short dress, skirt or shorts.

Over The Knee Boot with Short DressOver The Knee Boot with Short SkirtOver The Knee Boot with Shorts

Alternatively you can dress down this look by opting for a low-heeled pair.